Ammonium Chloride → HCID 86646304, compound

HRID 1027136Notes

Reaction equation

HRID 1027136 reaction equation
[CH3:1][C:2]1(O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:4]2([CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]2)[CH2:3]1.O.C1(C)C(S(O)(=O)=O)=CC=CC=1.[Cl-].[NH4+]>C(Cl)Cl>[CH3:1][C:2]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:4]2([CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:6][CH2:5]2)[CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 67082928HCID 67082928, compound

Product 1

HCID 86646304HCID 86646304, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 1-methyl-1-hydroxyspiro[indane-3,4′-piperidine]-1′-carboxylate (0.140 g, 0.441 mmol) obtained in step 1 was dissolved in methylene chloride (2 mL), toluenesulfonic acid monohydrate (0.008 g, 0.044 mmol) was added, and the mixture was stirred at room temperature for 3 hr. Saturated aqueous ammonium chloride solution was added dropwise to the reaction mixture, and the mixture was extracted several times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (0.108 g, 81%).

Workup

  1. extractionthe mixture was extracted several times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2b84a62b41144231829142f49ac6e675
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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